Patent GB-1029045-A (GB)
Title: New hydroxyaryl-pyrimidines,process for their preparation and their use
IPC: C07D239/26
Filed: 1964-04-30
Abstract: New hydroxyaryl pyrimidines of Formula (2) <FORM:1029045/C4-C5/1> in which A, A1 and A11 are the same or different and represent a benzene or naphthalene nucleus linked directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxy group in vicinal position to the bond to the pyrimidine ring; R1, R11 and R111 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthalene residue bound directly through a cyclic carbon atom to the pyrimidine ring; a=1, 2 or 3 and b, c, d, e and f each equals 0, 1 or 2 the sum a+b+c+d+e+f being 3, are used for the protection of organic materials from the effects of heat or light, in particular ultra-violet light.  The nuclei A, A1 and A11 may carry in addition to the o-hydroxy group, substituents such a halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2,3-epoxypropoxy, alkyl, alkenyl, sulphonic, carboxyl or acyl groups or carboxy alkoxy groups which may be free or esterified.  The new compounds may be incorporated into the substrate or in a "filter layer" to protect a substrate placed directly underneath it.  Among the materials which may be protected are soaps and substances containing waxes such as floor and furniture polishes and candles.ALSO:New hydroxyaryl pyrimidines of formula <FORM:1029045/C6-C7/1> in which A, A1 and A11 are the same or different and represent a benzene or naphthalene nucleus directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxy group in vicinal position to the bond to the pyrimidine ring; R1, R11 and R111 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthalene residue bound directly through a cyclic carbon atom to the pyrimidine ring; a = 1, 2 or 3 and b, c, d, e and f each equals 0, 1 or 2 the sum a + b + c + d + e + f being 3 are used for the protection of organic materials from the effects of heat or light, in particular ultraviolet light.  The nuclei A, A1 and A11 may carry in addition to the o-hydroxy group, substituents such as halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2, 3-epoxypropoxy, alkyl, alkenyl, sulphonic, carboxyl or acyl groups or carboxy alkoxy groups which may be free or esterified. The new compounds may be incorporated into the substrate or in a "filter layer" to protect a substrate placed directly underneath it.  Among the materials which may be protected are hairs, pelts, and hides and also leather made from hides by natural or chemical tanning.ALSO:The invention comprises hydroxyaryl pyrimidines of formula <FORM:1029045/C2/1> in which A, A1 and A11 are the same or different and represent a benzene or naphthalene nucleus linked directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxyl group in vicinal position to the bond to the pyrimidine ring; R1, R11 and R111 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthalene residue bound directly through a cyclic carbon atom to the pyrimidine ring; a = 1, 2 or 3 and b, c, d, e and f each equals 0, 1 or 2, the sum a+b+c+d+e+f being 3.  The nuclei A, A1 and A11 may carry, in addition to the 0-hydroxy group, substituents such as halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2,3-epoxy-propoxy, alkyl, alkenyl, sulphonic acid, carboxyl or acyl groups or carboxyalkoxy groups which may be free or esterified.  A preferred class of compounds are those of formula <FORM:1029045/C2/2> in which T is a hydrogen or chlorine atom or an alkyl or phenyl group; V a hydrogen or chlorine atom or an alkyl or phenyl group or a benzene residue of formula <FORM:1029045/C2/3> in which U10 stands for an alkyl group or for a group of formula-OQ2 and Q, Q1 and Q2 are the same or different, and each represents a hydrogen atom, an alkyl, alkenyl, hydroxyalkyl, carbalkoxyalkyl or phenylalkyl group, at least one of the two symbols Q and Q1 representing a hydrogen atom.  The new hydroxyaryl pyrimidines are obtained by known methods, e.g. by reacting in an anhydrous medium in the presence of a Friedel-Crafts catalyst, especially aluminium chloride, and in an inert organic solvent, halogeno-pyrimidines of the Formula <FORM:1029045/C2/4> in which a is 1, 2 or 3 and d, e and f are 0, 1 or 2, the sum (a+d+e+f) being 3 with compounds of the benzene or naphthalene series containing a hydroxyl group, which may be etherified, in vicinal position to the pyrimidine ring, in approximately equimolar amounts.  During the reaction the etherified hydroxy group, if present, is converted to a hydroxy group.  Numerous examples are given of starting materials and products.ALSO:New hydroxyaryl pyrimidines of formula <FORM:1029045/C3/1> in which A, A1 and A11 are the same or differen and represent a benzene or naphthalene nucleus linked directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxy group in vicinal position to the bond to the pyrimidine ring; R1, R11 and R111 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthalene residue bound directly through a cyclic carbon atom to the pyrimidine ring; a=1,2 or 3 and b, c, d, e and f each equals 0, 1 or 2 the sum a+b+c+d+e+f being 3, are used for the protection of organic materials from the effects of heat or light, in particular ultra-violet light.  The nuclei A, A1 and A11 may carry in addition to the o-hydroxy group, substituents such as halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2 3-epoxypropoxy, alkyl, alkenyl, sulphonic, carboxyl or acyl groups or carboxy alkoxy groups which may be free of esterified.  The new compounds may be incorporated into the substrate or in a "filter layer" to protect a substrate placed directly underneath it.  Among the materials which may be protected are (a) lacquers and films of cellulose esters, nitrocellulose, vinyl acetate, polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride and vinylidene chloride, alkyd lacquers, polyethylene, polypropylene, polyamides, polyacrylonitrile, polyesters, regenerated cellulose or acetyl cellulose; (b) natural or synthetic resins, e.g. epoxy resins, polyester resins, vinyl resins, polystyrene resins, alkyl resins, aldehyde resins such as formaldehyde condensation products with phenol, urea or melamine; and (c) fibres and filaments of natural cellulose materials or semi-synthetic materials such as rayon or viscose rayon, advantageously by incorporation in the spinning mass.  In the examples a compound of the general formula given above is incorporated in (a) a film prepared from acetonic acetyl cellulose solution; (b) TiO2 pigmented polyamide in chip form which is subsequently formed into filaments; (c) polyvinyl chloride foil, (d) polyethylene foil, (e) a polypropylene panel, and (f) a panel formed from a polyester resin based on phthalic acid, maleic acid and ethylene glycol.ALSO:New hydroxyaryl pyrimidines of formula <FORM:1029045/A5-A6/1> in which A, A1 and A11 are the same or different and represent a benzene or naphthalene nucleus linked directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxy group in vicinal position to the bond to the pyrimidine ring; R1, R11 and R111 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthaleneresidue bound directly through a cyclic carbon atom to the pyrimidine ring; a = 1, 2, or 3 and b, c, d, e and f each equals 0, 1 or 2 the sum a + b + c + d + e + f being 3, are used for the protection of organic materials from the effects of heat or light, in particular ultra-violet light.  The nuclei A, A1 and A11 may carry in addition to the o-hydroxy group, substituents such as halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2, 3-epoxypropoxy, alkyl, alkenyl, sulphonic, carboxyl or acyl groups or carboxy alkoxy groups which may be free or esterified.  The new compounds may be incorporated into the substrate or in a "filter layer" to protect a substrate placed directly underneath it.  Among the materials which may be protected are perfumes, skin and face creams, powders, repellants and especially sunburn oils and creams.ALSO:New hydroxyaryl pyrimidines of formula <FORM:1029045/D1-D2/1> in which A, A1 and A11 are the same or different and represent a benzene or naphthalene nucleus linked directly through a cyclic carbon atom to the pyrimidine ring and which contain a hydroxy group in vicinal position to the bond to the pyrimidine ring; R, R1, R11 and R11 are the same or different and each represents a hydrogen or halogen atom, an alkyl group or a benzene or naphthalene residue bound directly through a cyclic carbon atom to the pyrimidine ring; a = 1, 2 or 3 and b, c, d, e and f each equals 0, 1 or 2 the sum a + b + c + d + e + f being 3, are used for the protection of organic materials from the effects of heat or light, in particular ultra-violet light.  The nuclei A, A1 and A11 may carry in addition to the o-hydroxy group, substituents such as halogens or alkoxy, hydroxyalkyl, alkenyloxy, phenyloxy, 2, 3-epoxypropoxy, alkyl, alkenyl, sulphonic, carboxyl or acyl groups or carboxy alkoxy groups which may be free or esterified. The new compounds may be incorporated into the substrate or in a "filter layer" to protect a substrate placed directly underneath it. Among the materials which may be protected are textile materials in the form of fibres, filaments, yarns, woven or knitted fabrics or felt consisting of natural materials of animal origin such as wool or silk, or of vegetable origin such as cotton, hemp, flax, linen, jute and ramie.  They may also be used for the protection of pulps used in the manufacture of paper, e.g. hollander pulps, and of paper, cardboard and hardboard.  In add